Dimethylamine → HCID 25183063, compound

HRID 1746765Notes

Reaction equation

HRID 1746765 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][C:16]=3[CH3:23])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[CH3:27][NH:28][CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C(Cl)Cl>[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:28]([CH3:29])[CH3:27])=[CH:17][C:16]=3[CH3:23])=[O:13])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 2724942TriacetoxyborohydrideHCID 59446872HCID 59446872, compound2×

Product 1

HCID 25183063HCID 25183063, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-((cyclopropylmethyl)(propyl)amino)-N-(4-formyl-2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 29, 100 mg; 0.28 mmol) in DCM (5 ml) was treated with dimethylamine (Aldrich, 0.25 ml, 2M in THF; 0.5 mmol) followed by polymer supported triacetoxy borohydride (150 mg). After stirring for 18 hours the mixture was filtered and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with petroleum ether containing increasing amounts of EtOAc to give the title compound as an off-white solid.

Workup

  1. filtrationwas filtered
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by column chromatography (silica)
  4. washeluting with petroleum ether containing
  5. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-709647be9d5d4b6a89562dfc002019f6
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

Loading…